Acetic Anhydride → HCID 89783360, compound

HRID 1056179Notes

Reaction equation

[C:1]([NH:5][C:6]1[C:7]([CH3:26])=[N:8][C:9]2[C:14]([N:15]=1)=[C:13]([C:16]1[NH:24][C:23]3[CH2:22][CH2:21][NH:20][C:19](=[O:25])[C:18]=3[CH:17]=1)[CH:12]=[CH:11][CH:10]=2)([CH3:4])([CH3:3])[CH3:2].[CH3:27][C:28](OC(C)=O)=[O:29]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:28]([N:20]1[CH2:21][CH2:22][C:23]2[NH:24][C:16]([C:13]3[CH:12]=[CH:11][CH:10]=[C:9]4[C:14]=3[N:15]=[C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:7]([CH3:26])=[N:8]4)=[CH:17][C:18]=2[C:19]1=[O:25])(=[O:29])[CH3:27]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (193) (0.13 g, 0.37 mmol), DMAP (0.45 g, 3.75 mmol), and Ac2O (0.35 mL, 3.75 mmol) in pyridine (2 mL) was stirred at 50° C. in 24h. The reaction mixture was cooled, concentrated to dryness, purified by ISCO (0-30% EtOAc/DCM) to give the title compound (33 mg, 22%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.11 (1H, br. s.), 7.75-7.88 (1H, m), 7.54-7.67 (1H, m), 7.35 (1H, t, J=7.8 Hz), 7.30 (1H, d, J=2.2 Hz), 6.01 (1H, s), 4.14 (2H, t, J=6.3 Hz), 2.94 (2H, t, J=6.4 Hz), 2.55 (3H, s), 2.44 (3H, s), 1.56 (9H, s). m/z (ESI, +ve) 392.0 (M+H)+.

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated to dryness
custompurified by ISCO (0-30% EtOAc/DCM)

Sources & evidence

ORD record: ord-55a156b605f34c49b05dae4c324716d0
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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